2,6-Diacetylpyridine → HCID 22171925, compound

2,6-Diacetylpyridine (4.04 g, 24.7 mmol) and 2,6-difluoroaniline (3.2 g, 24.7 mmol) were dissolved in 50 ml of toluene. To this solution, molecular sieves (4 Å) were added. After standing for 5 days at room temperature, the mixture was filtered. The solvent was removed in vacuo. From the resulting mixture of 2,6-diacetylpyridine, monoimine, and diimine. Most of the 2,6-diacetylpyridine was removed by sublimation in vacuo at 80-90° C. The residue contained based on 1H-NMR data 0.35 mmol 2,6-diacetylpyridine , 1.28 mmol diimine and 5.46 mmol monoimine. This mixture was reacted with 162 mg (1.28 mmol) FeCl2 in 10 ml THF to remove the diimine. After stirring for 16 h at room temperature, the solvent was removed in vacuo. Toluene (50 ml) was added to the resulting mixture. The precipitated complex was filtered off over a small layer of silica, yielding a yellow solution. The solvent was removed in vacuo. Crystallisation from ethanol yielded 1.35 g of 2-[1-(2,6-difluorophenylimino)ethyl]-6-acetylpyridine (18) (19.8%).

1. additionTo this solution, molecular sieves (4 Å) were added
2. filtrationthe mixture was filtered
3. customThe solvent was removed in vacuo
4. additionFrom the resulting mixture of 2,6-diacetylpyridine, monoimine, and diimine
5. customMost of the 2,6-diacetylpyridine was removed by sublimation in vacuo at 80-90° C
6. customto remove the diimine
7. customthe solvent was removed in vacuo
8. additionToluene (50 ml) was added to the resulting mixture
9. filtrationThe precipitated complex was filtered off over a small layer of silica
10. customyielding a yellow solution
11. customThe solvent was removed in vacuo
12. customCrystallisation from ethanol

ORD record

ord-ea9cff734654463caa31963c33b7079e

Source dataset

uspto-grants-2007_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07238764B2